organic compounds
2-Amino-6-methylpyridinium 2-hydroxybenzoate
aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, cDepartment of Physics, Alagappa University, Karaikkudi 630 003, India, and dDepartment of Physics, The American College, Madurai 625 002, India
*Correspondence e-mail: israel.samuel@gmail.com, chakkaravarthi_2005@yahoo.com
In the title molecular salt, C6H9N2+·C7H5O3−, the cation is protonated at its pyridine N atom and and makes a dihedral angle of 16.26 (9)° with the plane of the six-membered ring of the anion. The six-membered ring makes a dihedral angle of 6.09 (3)° with the attached carboxylate group. In the anion, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif and a pair of N—H⋯O hydrogen bonds generates an R22(8) ring motif. In the crystal, the anions and cations are linked via N—H⋯O hydrogen bonds to form a tetramer.
Keywords: crystal structure; molecular salt; hydrogen bonding.
CCDC reference: 1478169
Structure description
Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996) and they are also known to exhibit non-linear optical (NLO) properties (Tomaru et al., 1991). Herein, we report on the synthesis and the of the title molecular salt. The title compound, Fig. 1, contains a 2-amino-6-methylpyridinium cation, which is protonated at atom N1, and 2-hydroxybenzoate which is deprotonated at its O2 atom. The geometric parameters are comparable with those reported for similar structures (Jin et al., 2000, 2001; Quah et al., 2010).
The benzene ring (C1–C6) of the anion makes a dihedral angle of 6.09 (3)° with the attached carboxylate (C7/O2/O3) group. The benzene and pyridine rings are inclined at an angle of 16.26 (9)°. In the anion, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif (Fig. 1). In the crystal, the anions and cations are connected by N—H⋯O hydrogen bonds generating an R22(8) ring motif (Fig. 2). Four pairs of anions and cations are linked by N—H⋯O hydrogen bonds (Table 1) to form a tetramer with an R44(16) ring motif (Fig. 3).
Synthesis and crystallization
2-Amino-6-picoline (0.54 g) and 2-hydroxybenzoic acid (0.69 g) in an equimolar ratio were mixed in acetone and the mixture was stirred for 3 h. A single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1478169
10.1107/S2414314616007471/bt4008sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007471/bt4008Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616007471/bt4008Isup3.cml
2-Amino-6-picoline (0.54 g) and 2 hydroxybenzoic acid (0.69 g) in an equimolar ratio were mixed in acetone and the mixture was stirred for 3 h. A single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation.
Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996) and they are also known to exhibit non-linear optical (NLO) properties (Tomaru et al., 1991). Herein, we report on the synthesis and the
of the title molecular salt. The title compound, Fig. 1, contains a 2-amino-6-methylpyridinium cation, which is protonated at atom N1, and 2-hydroxybenzoate which is deprotonated at its O2 atom. The geometric parameters are comparable with those reported for similar structures (Jin et al., 2000, 2001; Quah et al., 2010).The benzene ring (C1–C6) of the anion makes a dihedral angle of 6.09 (3)° with the attached carboxylate (C7/O2/O3) group. The benzene and pyridine rings are inclined at an angle of 16.26 (9)°. In the anion, an intramolecular O—H···O hydrogen bond generates an S(6) ring motif (Fig. 1). In the crystal, the anions and cations are connected by N—H···O hydrogen bonds generating an R22(8) ring motif (Fig. 3). Four pairs of anions and cations are linked by N—H···O hydrogen bonds (Table 1) to form a tetramer with an R44(16) ring motif (Fig. 3).
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound, viewed along the c axis. The hydrogen bonds (see Table 1) are shown as dashed lines and C-bound H atoms have been omitted for clarity. | |
Fig. 3. A partial view of the crystal packing of the title compound, showing the hydrogen-bonded tetramer. |
C6H9N2+·C7H5O3− | Dx = 1.333 Mg m−3 |
Mr = 246.26 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 9075 reflections |
Hall symbol: -I 4ad | θ = 2.6–27.3° |
a = 14.1096 (6) Å | µ = 0.10 mm−1 |
c = 24.6537 (11) Å | T = 293 K |
V = 4908.1 (4) Å3 | Block, colourless |
Z = 16 | 0.28 × 0.24 × 0.20 mm |
F(000) = 2080 |
Bruker Kappa APEXII CCD diffractometer | 2705 independent reflections |
Radiation source: fine-focus sealed tube | 1564 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω and φ scan | θmax = 27.1°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −17→18 |
Tmin = 0.974, Tmax = 0.981 | k = −18→15 |
33461 measured reflections | l = −31→31 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.079P)2 + 4.2162P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2705 reflections | Δρmax = 0.17 e Å−3 |
169 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (4) |
C6H9N2+·C7H5O3− | Z = 16 |
Mr = 246.26 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.10 mm−1 |
a = 14.1096 (6) Å | T = 293 K |
c = 24.6537 (11) Å | 0.28 × 0.24 × 0.20 mm |
V = 4908.1 (4) Å3 |
Bruker Kappa APEXII CCD diffractometer | 2705 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1564 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.981 | Rint = 0.041 |
33461 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 1 restraint |
wR(F2) = 0.191 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.17 e Å−3 |
2705 reflections | Δρmin = −0.18 e Å−3 |
169 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3466 (2) | 0.3614 (2) | 0.53227 (11) | 0.0800 (9) | |
H1 | 0.3287 | 0.3597 | 0.5686 | 0.096* | |
C2 | 0.4403 (2) | 0.3718 (3) | 0.51924 (13) | 0.1165 (15) | |
H2 | 0.4854 | 0.3779 | 0.5465 | 0.140* | |
C3 | 0.4674 (2) | 0.3733 (3) | 0.46571 (13) | 0.1088 (13) | |
H3 | 0.5311 | 0.3798 | 0.4568 | 0.131* | |
C4 | 0.4020 (2) | 0.3655 (2) | 0.42581 (12) | 0.0780 (8) | |
H4 | 0.4210 | 0.3666 | 0.3897 | 0.094* | |
C5 | 0.30732 (18) | 0.35571 (17) | 0.43851 (9) | 0.0585 (6) | |
C6 | 0.27839 (17) | 0.35353 (16) | 0.49277 (9) | 0.0544 (6) | |
C7 | 0.17649 (18) | 0.34951 (17) | 0.50774 (10) | 0.0599 (6) | |
C8 | 0.13374 (19) | 0.61715 (17) | 0.54553 (10) | 0.0614 (6) | |
C9 | 0.2265 (2) | 0.6006 (2) | 0.53459 (12) | 0.0730 (7) | |
H9 | 0.2712 | 0.6010 | 0.5623 | 0.088* | |
C10 | 0.2540 (2) | 0.5829 (2) | 0.48125 (12) | 0.0745 (8) | |
H10 | 0.3176 | 0.5717 | 0.4736 | 0.089* | |
C11 | 0.19078 (19) | 0.58161 (18) | 0.44066 (11) | 0.0670 (7) | |
H11 | 0.2104 | 0.5699 | 0.4053 | 0.080* | |
C12 | 0.09491 (17) | 0.59811 (17) | 0.45197 (10) | 0.0576 (6) | |
C13 | 0.0943 (2) | 0.6378 (2) | 0.59994 (11) | 0.0778 (8) | |
H13A | 0.1448 | 0.6403 | 0.6260 | 0.117* | |
H13B | 0.0504 | 0.5888 | 0.6099 | 0.117* | |
H13C | 0.0620 | 0.6977 | 0.5992 | 0.117* | |
N1 | 0.07022 (14) | 0.61524 (13) | 0.50402 (7) | 0.0560 (5) | |
H1B | 0.0115 | 0.6254 | 0.5113 | 0.067* | |
N2 | 0.02771 (16) | 0.59673 (17) | 0.41480 (8) | 0.0744 (7) | |
H2A | −0.0303 | 0.6066 | 0.4239 | 0.089* | |
H2B | 0.0419 | 0.5860 | 0.3814 | 0.089* | |
O1 | 0.24464 (16) | 0.35081 (17) | 0.39747 (7) | 0.0842 (6) | |
O2 | 0.11578 (12) | 0.35100 (14) | 0.46963 (7) | 0.0710 (5) | |
O3 | 0.15438 (14) | 0.34665 (16) | 0.55672 (7) | 0.0848 (6) | |
H1A | 0.1912 (12) | 0.351 (3) | 0.4121 (13) | 0.103 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0703 (18) | 0.121 (3) | 0.0491 (14) | 0.0083 (16) | −0.0032 (13) | −0.0042 (15) |
C2 | 0.068 (2) | 0.210 (5) | 0.071 (2) | 0.003 (2) | −0.0143 (16) | −0.015 (2) |
C3 | 0.0611 (18) | 0.187 (4) | 0.078 (2) | −0.001 (2) | 0.0049 (16) | −0.021 (2) |
C4 | 0.0699 (18) | 0.105 (2) | 0.0590 (16) | 0.0030 (15) | 0.0115 (13) | −0.0068 (15) |
C5 | 0.0649 (15) | 0.0631 (14) | 0.0475 (12) | 0.0037 (11) | 0.0001 (11) | −0.0051 (11) |
C6 | 0.0623 (14) | 0.0560 (13) | 0.0449 (12) | 0.0022 (10) | 0.0010 (10) | −0.0011 (10) |
C7 | 0.0691 (16) | 0.0600 (14) | 0.0507 (13) | −0.0006 (11) | 0.0066 (12) | 0.0029 (11) |
C8 | 0.0746 (17) | 0.0528 (13) | 0.0567 (14) | −0.0034 (11) | −0.0060 (12) | 0.0019 (11) |
C9 | 0.0693 (17) | 0.0729 (17) | 0.0769 (18) | 0.0000 (13) | −0.0128 (14) | −0.0029 (14) |
C10 | 0.0637 (16) | 0.0726 (18) | 0.087 (2) | 0.0004 (13) | 0.0039 (15) | −0.0033 (15) |
C11 | 0.0678 (16) | 0.0675 (16) | 0.0656 (15) | −0.0039 (12) | 0.0113 (13) | −0.0032 (12) |
C12 | 0.0634 (15) | 0.0533 (13) | 0.0562 (14) | −0.0036 (11) | 0.0045 (11) | 0.0005 (10) |
C13 | 0.101 (2) | 0.0790 (19) | 0.0537 (15) | 0.0022 (15) | −0.0050 (14) | 0.0003 (13) |
N1 | 0.0612 (12) | 0.0571 (11) | 0.0498 (11) | −0.0018 (8) | 0.0038 (9) | 0.0008 (9) |
N2 | 0.0680 (14) | 0.1037 (18) | 0.0515 (12) | −0.0038 (12) | 0.0052 (10) | −0.0041 (11) |
O1 | 0.0745 (14) | 0.1301 (18) | 0.0479 (10) | 0.0021 (12) | −0.0030 (10) | −0.0113 (11) |
O2 | 0.0595 (11) | 0.0935 (14) | 0.0599 (11) | −0.0034 (9) | −0.0014 (8) | −0.0029 (9) |
O3 | 0.0791 (13) | 0.1217 (17) | 0.0536 (11) | 0.0050 (11) | 0.0131 (9) | 0.0169 (10) |
C1—C2 | 1.368 (4) | C8—C13 | 1.481 (4) |
C1—C6 | 1.374 (3) | C9—C10 | 1.394 (4) |
C1—H1 | 0.9300 | C9—H9 | 0.9300 |
C2—C3 | 1.374 (4) | C10—C11 | 1.341 (4) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C4 | 1.353 (4) | C11—C12 | 1.401 (4) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.379 (4) | C12—N2 | 1.319 (3) |
C4—H4 | 0.9300 | C12—N1 | 1.351 (3) |
C5—O1 | 1.346 (3) | C13—H13A | 0.9600 |
C5—C6 | 1.399 (3) | C13—H13B | 0.9600 |
C6—C7 | 1.485 (3) | C13—H13C | 0.9600 |
C7—O3 | 1.248 (3) | N1—H1B | 0.8600 |
C7—O2 | 1.272 (3) | N2—H2A | 0.8600 |
C8—C9 | 1.357 (4) | N2—H2B | 0.8600 |
C8—N1 | 1.361 (3) | O1—H1A | 0.835 (10) |
C2—C1—C6 | 121.3 (3) | C8—C9—H9 | 120.4 |
C2—C1—H1 | 119.4 | C10—C9—H9 | 120.4 |
C6—C1—H1 | 119.4 | C11—C10—C9 | 121.4 (3) |
C1—C2—C3 | 119.7 (3) | C11—C10—H10 | 119.3 |
C1—C2—H2 | 120.1 | C9—C10—H10 | 119.3 |
C3—C2—H2 | 120.1 | C10—C11—C12 | 119.4 (3) |
C4—C3—C2 | 120.5 (3) | C10—C11—H11 | 120.3 |
C4—C3—H3 | 119.8 | C12—C11—H11 | 120.3 |
C2—C3—H3 | 119.7 | N2—C12—N1 | 118.5 (2) |
C3—C4—C5 | 120.2 (3) | N2—C12—C11 | 123.6 (2) |
C3—C4—H4 | 119.9 | N1—C12—C11 | 117.9 (2) |
C5—C4—H4 | 119.9 | C8—C13—H13A | 109.5 |
O1—C5—C4 | 118.1 (2) | C8—C13—H13B | 109.5 |
O1—C5—C6 | 121.7 (2) | H13A—C13—H13B | 109.5 |
C4—C5—C6 | 120.1 (2) | C8—C13—H13C | 109.5 |
C1—C6—C5 | 118.1 (2) | H13A—C13—H13C | 109.5 |
C1—C6—C7 | 120.3 (2) | H13B—C13—H13C | 109.5 |
C5—C6—C7 | 121.4 (2) | C12—N1—C8 | 123.2 (2) |
O3—C7—O2 | 123.2 (2) | C12—N1—H1B | 118.4 |
O3—C7—C6 | 118.9 (2) | C8—N1—H1B | 118.4 |
O2—C7—C6 | 117.9 (2) | C12—N2—H2A | 120.0 |
C9—C8—N1 | 118.8 (2) | C12—N2—H2B | 120.0 |
C9—C8—C13 | 125.2 (3) | H2A—N2—H2B | 120.0 |
N1—C8—C13 | 115.9 (2) | C5—O1—H1A | 106 (2) |
C8—C9—C10 | 119.1 (3) | ||
C6—C1—C2—C3 | −0.8 (6) | C1—C6—C7—O2 | 173.6 (3) |
C1—C2—C3—C4 | 0.6 (7) | C5—C6—C7—O2 | −2.1 (3) |
C2—C3—C4—C5 | −0.1 (6) | N1—C8—C9—C10 | 0.5 (4) |
C3—C4—C5—O1 | 178.2 (3) | C13—C8—C9—C10 | −179.4 (3) |
C3—C4—C5—C6 | −0.2 (4) | C8—C9—C10—C11 | −0.2 (4) |
C2—C1—C6—C5 | 0.4 (5) | C9—C10—C11—C12 | −0.2 (4) |
C2—C1—C6—C7 | −175.4 (3) | C10—C11—C12—N2 | −178.9 (3) |
O1—C5—C6—C1 | −178.3 (3) | C10—C11—C12—N1 | 0.3 (4) |
C4—C5—C6—C1 | 0.1 (4) | N2—C12—N1—C8 | 179.2 (2) |
O1—C5—C6—C7 | −2.4 (4) | C11—C12—N1—C8 | 0.0 (3) |
C4—C5—C6—C7 | 175.9 (2) | C9—C8—N1—C12 | −0.4 (4) |
C1—C6—C7—O3 | −5.0 (4) | C13—C8—N1—C12 | 179.5 (2) |
C5—C6—C7—O3 | 179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.84 (1) | 1.77 (2) | 2.544 (3) | 152 (3) |
N1—H1B···O2i | 0.86 | 1.89 | 2.745 (3) | 177 |
N2—H2A···O3i | 0.86 | 1.93 | 2.781 (3) | 169 |
N2—H2B···O3ii | 0.86 | 2.00 | 2.836 (3) | 163 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) y−1/4, −x+3/4, z−1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.835 (10) | 1.774 (18) | 2.544 (3) | 152 (3) |
N1—H1B···O2i | 0.86 | 1.89 | 2.745 (3) | 177 |
N2—H2A···O3i | 0.86 | 1.93 | 2.781 (3) | 169 |
N2—H2B···O3ii | 0.86 | 2.00 | 2.836 (3) | 163 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) y−1/4, −x+3/4, z−1/4. |
Experimental details
Crystal data | |
Chemical formula | C6H9N2+·C7H5O3− |
Mr | 246.26 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 293 |
a, c (Å) | 14.1096 (6), 24.6537 (11) |
V (Å3) | 4908.1 (4) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.28 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.974, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33461, 2705, 1564 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.191, 1.05 |
No. of reflections | 2705 |
No. of parameters | 169 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
References
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Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996) and they are also known to exhibit nonlinear optical (NLO) properties (Tomaru et al., 1991). Herein, we report on the synthesis and the crystal structure of the title molecular salt. The title compound, Fig. 1, contains a 2-amino-6-methylpyridinium cation, which is protonated at atom N1, and 2-hydroxybenzoate which is deprotonated at its O2 atom. The geometric parameters are comparable with those reported for similar structures (Jin et al., 2000; Jin et al., 2001; Quah et al., 2010).
The benzene ring (C1—C6) of the anion makes a dihedral angle of 6.09 (3)° with the attached carboxylate (C7/O2/O3) group. The benzene and pyridine rings are inclined at an angle of 16.26 (9)°. In the anion, an intramolecular O—H···O hydrogen bond generates an S(6) ring motif (Fig. 3). and an anion and a cation are connected by of N—H···O hydrogen bonds generating an R22(8) ring motif (Bernstein et al., 1995) (Fig. 3). Four pairs of anions and cations are linked by N—H···O hydrogen bonds (Table 2) to form a tetramer with an R44(16) ring motif (Fig. 2).